


Do Knot Get In A Strangers Car

by KnottheWolf



Series: Requests [4]
Category: Teen Wolf (TV)
Genre: Alpha Derek Hale, Alternate Universe - Sugar Daddy, Alternate universe - Mafia, Bondage, Boypussy, Boypussy Stiles Stilinski, Come Inflation, Feminization, Knotting, Light Dom/sub, M/M, Mob Boss Derek Hale, Pet Names, Plot What Plot/Porn Without Plot, Smut, Somnophilia, Vibrators, spreader bar
Language: English
Status: Completed
Published: 2020-09-20
Updated: 2020-09-20
Packaged: 2021-03-07 21:20:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,342
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26554249
Author URL: https://archiveofourown.org/users/KnottheWolf/pseuds/KnottheWolf
Summary: Prompt: Mob boss Derek sees Stiles and instantly wants him to be his, and he'll do anything to make Stiles see it too.~~Mob Boss Derek fucking his kept Boy Stiles all day everyday they don't even use plugs anymore. Boypussy, Feminization, Somnophilia, Sugar Daddy Derek
Relationships: Derek Hale/Stiles Stilinski
Series: Requests [4]
Series URL: https://archiveofourown.org/series/1926433
Comments: 18
Kudos: 947





	Do Knot Get In A Strangers Car

**Author's Note:**

> I threw both of these together because they both wanted Mob Boss Derek Hale.

When Derek first met Stiles Stilinski, the man had run into him because he wasn’t looking and where Derek thought he was going to completely ignore the mess of coffee he made on Derek’s shirt, or yell at the man he was wrong. Instead, Stiles had looked down at Derek’s shirt before his face went entirely red and he started pulling napkins out of his bag and pushing them against Derek’s chest. While repeatedly chanting the phrase, “I’m sorry. I’m sorry. Oh god, I am so fucking sorry!” After that he offered to pay for Derek’s coffee as well as dry cleaning which had Derek raising an eyebrow at the younger man until he went silent, and his cheeks were red. Suddenly there’s a scent in the air and Derek almost flashes red eyes at the poor boy before pulling himself back. 

This man smells wonderful. He smells like mate, mine, and ours. Which has Derek leaning forward before pulling himself back and straightening his shirt off.

“There’s no need to worry, I can deal with it myself.” Derek tells the stranger, his voice coming out rougher than he wants it to.

“Wh-no! Dude, I ruined your shirt, it was perfectly clean before I came and slammed right into you.” The man’s hands flail around a bit as he tries to explain his point, before he pulls them in and links his fingers together. Like he was trying to hide the fact that he had ADHD, but Derek could smell the medication on him as well as that sweet scent that had his eyes going a little hazy with lust.

“Don’t call me dude.” Derek raises an imperious eyebrow, “My name is Derek Hale.”

“Derek, nice to meet you. I’m Stiles Stilinski.”

After that, Derek looked up everything he could find about Stiles Stilinski. It probably crossed a few lines but he just had to know who this man was, and being the head of a mob made finding these things easy. No one asked questions or second guessed his judgement, and since he was a born Alpha werewolf there was an even more level of fear that he brought to the table. When he had everything in his hand it made it easier to find Stiles, to make them bump into one another on the streets again so he could watch Stiles get flustered under his heavy stare and a blush on those cheeks. And that scent, God, that wonderful scent that drove him mad with lust. He wanted to grab Stiles and tie him up to his bed, wanted to slowly open him up with his fingers and toys before slowly fucking the man into his sheets. He’d take his sweet time first, open that sweet hole between Stiles’s legs and then later on when he’s gotten use to it, he’d fuck Stiles like an animal. Derek would let that primal, animalistic need inside of him loose and he’d fuck and knot the pretty boys ass, keep him in his bed all day until the only thing he remembers is Derek’s knot in his ass.

The only thing he needed to do was convince Stiles to be his.

______________

“Wow.” 

Derek turned his head to watch as Stiles surveyed the room with wide eyes and his jaw to the ground. Stiles was wearing an ill fitted suit that had Derek wanting to take him to the nearest tailer, but after doing his research on Stiles he found the man simply didn’t have the money to afford this kind of stuff. Meaning his suit was either borrowed from a friend or rented some where, Derek would just have to deal with the wrinkled clothes and rumpled shirts for now. Until he could have Stiles as his own, then his boy would never have to worry about such mundane things. Derek would pamper him, would buy him all the things he needed to wear. Of course he would want Stiles to walk around naked most of the time, make it easier for Derek to slip his cock out of his pants and fuck Stiles against any and every surface.

But he also thought about buying nice clothes for Stiles and a few suits, perhaps even a dress if he could convince Stiles to wear one. He’d throw out all of Stiles’ old ratty underwear and buy him some nice silk lace panties, have Stiles spread out on the bed so he could shave him of his his leg hair before pressing kisses up the younger man’s legs. Press his teeth against the creamy white inside of Stiles’s thighs and mark them black and blue, before fucking him.

“Do you like it?” Derek pulls a chair out for Stiles and waits until the man is sitting down to push the chair in. Letting his fingers slide against the back of his shirt so he can leave his scent on Stiles.

“It’s uh…jeez, I feel so under dressed here and we’re both wearing suits.”

Hardly, Derek thinks to himself. Stiles is wearing something you’d put on a monkey or a dog for entertainment, or perhaps your younger sibling if you were going to a family wedding. While Derek on the other hand was wearing a finely tailored suit from a man that only takes selective clients and hand makes everything. Derek’s suit was like a sports car while Stiles couldn’t even compare.

“You look fine, Stiles.” Derek smiles over his menu, wanting to calm the younger mans nerves.

“Are you sure? Because I feel like I shouldn’t even be here, much less be sitting here with you. Everyone keeps looking over at us.” He watches as Stiles wipes his sweaty palms on his pant legs and looks down at his hands while his face turns white like a paper.

“Which is why I reserved the private box for us.” Derek leans over and pulls on a rope, which has thick red curtains close off the room they’ve been seated in. When he notes, Stiles’s nerves have calmed down he moves them forward to the meal. Watching with something akin to fond as Stiles bumbles over the menu and getting more and more redder as he looks at the choices.

“How come the prices aren’t listed?”

Raising an eyebrow, Derek takes a sip of his whiskey, “Kitten, this restaurant is not only five stars but you have to call five weeks ahead because tis so high in demand. Not only that but you have to call five weeks ahead just to get a table, its a good thing I know the owner.”

Stiles blushes at the nickname and Derek wants nothing more than to eat him up, “Right. Um, so I guess I shouldn’t worry about the prices?”

“Order whatever you want, kitten.”

When the food comes, Stiles is a bit looser with his tongue as he’s had a glass of wine in him. Derek finds himself grinning more than he ever has in his life, and leans in as he listens to every wild story Stiles has to tell him. Never wanting the younger man to stop talking. They finish the main course and have desert which Derek takes great pleasure in watching Stiles lick cream off of a spoon.

“So Stiles, college must be pretty expensive.” 

The younger man pauses and finishes the spoonful in his mouth, nodding his head as he says, “It can be.”

“I think I might have a proposition for you then.”

______________

Pushing open the door to his private chambers, Derek stops momentarily when he sees Stiles fast a sleep on his bed. Wearing creamy white panties with frills at the edges, along with stockings and a garter belt to go along with it, and to top it all off he was even wearing a matching bra that was fitted to cup him chest perfectly. Hands bound together with leather cuffs and his legs spread wide from the bar Derek left on. There was the soft sound of buzzing in the air from the vibrator Derek left on low before he left to attend a meeting, a smirk curled up Derek’s face slowly as he spotted the wet patch between Stiles’s legs. His boy was fast asleep but his cunt was still aching and wet for Derek’s cock. And what kind of Alpha is he to deny his mate their pleasure.

Slipping out of his jacket and setting it on his chair before kicking off his shoes and getting on the bed, Derek unzipped the front part of his pants and pulled his cock out. The scent of Stiles’s cum and slick in the air already had him hard and ready to fuck his mate into the sheets. He paused when he noticed Stiles was sleeping but then kept moving forward. Not letting that stop him from yanking down the white panties Stiles was wearing, remaking the vibrator, and pushing his cock inside of that sweet cunt. Groaning as Stiles’s cunt clenches around his cock even when his boy is sleeping. 

Derek works his hips fast and hard, still riled up from the meeting he had earlier. He had wanted nothing more than to claw someone’s face off or rip out a few throats, but he learned that was not a productive way to lead. And instead when he got pent up with anger he would use that rage to push Stiles to the bed and fuck him until he was a sobbing mess of tears. Hand sized bruises on his hips, and teeth marks in his skin, maybe a swollen lip from where Derek was sucking too hard. Stiles learned early on not to stop or fight back, and was more than happy to spread his legs and have Derek fill that creamy cunt with his cum. Stiles, his perfect little kitten, his sweet baby boy. Snarling, Derek let his claws and fangs come out to play as he snapped his hips harshly, the bed rocking with the strength of his hips and Stiles’s body bouncing underneath him.

“Fuck, Stiles.” Derek grunts, pushing Stiles down further so his cock can press up against that little spot that always has his boy screaming.

And it does, Stiles wakes up slowly at first and then wakes with a beautiful cry on his lips. Hands clinging to the sheets immediately as he trips to hold himself steady, but to no use as Derek fucks like a damn machine.

“Derek! Alpha! Oh!” Stiles cries, shaking like a leaf as his pussy clenches around Derek’s cock.

Grunting, the Alpha fucks his mate harshly until he can smell his arousal closing in, “Gonna breed that sweet little cunt of yours, kitten. Did you miss your Alpha today?”

“Yes, missed you-missed you.” Stiles whines underneath him. “Knot me, please Alpha. I need it so badly.”

“Well, I was going to save it for later, but if my baby wants my knot now I can’t possible refuse them.” Derek grins, letting his hips slow down a little so he can work his knot inside of Stiles’s pussy.

Watching with rapt attention as each time he pushes the bulbous girth, Stiles clenches and squeezes around it like he’s trying to milk his knot. His little bitch is always hungry to be filled with Derek’s come, and he’s more than happy to give it to his mate. Loves watching as his come drips down between Stiles’s legs and makes a mess. Doesn’t bother cleaning up because he knows it’ll only be a matter of minutes before he’s fucking Stiles again and again.

“Mhh-mhh! Alpha! I’m so close, please. Let me come, please, Alpha?”

“Of course you can come beautiful,” Derek rakes claws down Stiles’s back and watches the red marks burn angrily. “But only if you come on my knot.”

Stiles nods his head furiously, “Yes, Alpha.”

He moans and whimpers needy, arching his back and pushing his hips as best as he can against Derek’s cock. The older man smirking as he watches Stiles try to work the orgasm out of himself. Derek’s knot swelling until he has to force it inside of Stiles’s sweet cunt just to fuck his boy.

“God, I love this little cunt of yours baby. So fucking perfect and wet for me.” Derek kisses pale, mole dotted shoulders and then presses fangs into them.

And as quickly as it started, Stiles was crying out again as he came all over Derek’s cock. Gushing over his thighs and making a mess on Derek’s pants which had the older man pushing himself on top of Stiles so he could snap his hips harshly until he could reach his own orgasm. Stiles making these sweet little mewls beneath him, and Derek craved those little noises as he worked another orgasm out of that sweet cunt before finally coming. Huffing and grunting, Derek laid himself on top of Stiles’s limp body. Licking a wet strip up Stiles’s throat and kissing all over that tantalizing skin and keeping a hold on Stiles’s hips.

“So fucking beautiful, my sweet little kitten.” Derek whispers, teething at Stiles’s lips before sucking on those as well.

“Are you finished with work now, Alpha?” Stiles sighs out, sounding completely drunk and high off of his orgasm.

“No, baby, I’m not.” Derek watches as a frown and a sour note takes hold of Stiles’s scent. “But, if you’re good enough. I’ll let you sit on my knot while I work in my office.”

Stiles mans, and Derek know he’s got his boy sold on the idea, “Please, Alpha. I’ll be good. I promise.”

“I know you will baby boy.” Derek kisses his lips, and settles down. Waiting until his knot goes down.

He hasn’t yet decided if he wants to fuck Stiles again or have him ride his cock while Derek’s in his office, but for now he’ll settle with Stiles’s sweet pussy milking his knot. Pressing kisses over Stiles’s skin until his mate is sleepy and warm in his arms, and the two of them can settle for a nap.

**Author's Note:**

> Comments and Kudos are always loved!!
> 
> Prompt Request Form:
> 
> https://forms.gle/zxcRfpSkK3sK3DwS9


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